Synthesis of 1,3,5-Tris[(4 '-ethynylphenyl)ethynyl]benzene
Chen Qiuyan; Ma Yuwen; Wang Chengyun; Shen Yongjia; ,
| HERO ID | 6928671 |
|---|---|
| In Press | No |
| Year | 2012 |
| Title | Synthesis of 1,3,5-Tris[(4 '-ethynylphenyl)ethynyl]benzene |
| Authors | Chen Qiuyan; Ma Yuwen; Wang Chengyun; Shen Yongjia; , |
| Journal | Youji Huaxue / Chinese Journal of Organic Chemistry |
| Page Numbers | 1526-1532 |
| Abstract | Several synthetic routes were designed to prepare 1,3,5-tris[(4-ethynylphenyl)ethynyl]benzene. The synthetic routes and reaction conditions were contrasted and discussed, when multiple Sonogashira reactions were occurred between multifunctional alkyne-terminal compounds and aromatic bromine compounds, the different substitution degree compounds with similar polarity were obtained, and they were difficult to separate. Whereas the reactions between multifunctional alkyne-terminal compounds and aromatic iodine compounds can avoid this situation. 1,3,5-Tribromobenzene reacted with 3-methylbutynol to afford 1,3,5-tris(3'-hydroxy-3'-methyl-but-1'-ynyl)benzene, then 1,3,5-triethynylbenzene was obtained by the cleavage reaction of the compound in presence of potassium hydroxide and toluene. On the other hand, using 4-iodoaniline and trimethyl silyl acetylene as raw materials, 4-trimethylsiylethynyl iodobenzene was synthesized by diazo reaction and halogenation. Therefore, 1,3,5-tris[(4'-ethynylphenyl)ethynyl]benzene was prepared by the cleavage reaction of the 1,3,5-triethynylbenzene and 4-trimethylsiylethynyl iodobenzene. The structures of the target compound and intermediates were confirmed by H-1 NMR, C-13 NMR techniques and element analysis. |
| Doi | 10.6023/cjoc201203007 |
| Wosid | WOS:000308837200024 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |